I have been trying to find JFK-SFO award tickets for 25k for a 4 day weekend in either August-Sept-Oct (I think that is being very flexible)...but EVERY SINGLE DAY of those 3 months is MEDIUM at 40k..is this one of those routes where I have a better chance at winning the Mega Millions then snagging 25k seats?

Here is where KVS comes in useful.
You can put in your search and hit Ctrl+page down and just go through 2 months in about 15 min.
The other problem is the lack of Plat status. Once you hit PM, just book at 40 and keep searching for a 25 to open up.